US20210009803A1 - Storage Stable and Curable Resin Compositions - Google Patents

Storage Stable and Curable Resin Compositions Download PDF

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Publication number
US20210009803A1
US20210009803A1 US16/981,334 US201916981334A US2021009803A1 US 20210009803 A1 US20210009803 A1 US 20210009803A1 US 201916981334 A US201916981334 A US 201916981334A US 2021009803 A1 US2021009803 A1 US 2021009803A1
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Prior art keywords
resin composition
storage stable
silane
curable resin
composition according
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US16/981,334
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English (en)
Inventor
Christian Beisele
Hubert Wilbers
Daniel Baer
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Huntsman Advanced Materials Licensing Switzerland GmbH
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Huntsman Advanced Materials Licensing Switzerland GmbH
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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
    • C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
    • C08G59/68—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the catalysts used
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J3/00—Processes of treating or compounding macromolecular substances
    • C08J3/20—Compounding polymers with additives, e.g. colouring
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K3/00—Use of inorganic substances as compounding ingredients
    • C08K3/34—Silicon-containing compounds
    • C08K3/36—Silica
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/54—Silicon-containing compounds
    • C08K5/541—Silicon-containing compounds containing oxygen
    • C08K5/5435—Silicon-containing compounds containing oxygen containing oxygen in a ring
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
    • C08L83/10—Block- or graft-copolymers containing polysiloxane sequences
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L2205/00—Polymer mixtures characterised by other features
    • C08L2205/02—Polymer mixtures characterised by other features containing two or more polymers of the same C08L -group
    • C08L2205/025—Polymer mixtures characterised by other features containing two or more polymers of the same C08L -group containing two or more polymers of the same hierarchy C08L, and differing only in parameters such as density, comonomer content, molecular weight, structure
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L2205/00—Polymer mixtures characterised by other features
    • C08L2205/03—Polymer mixtures characterised by other features containing three or more polymers in a blend

Definitions

  • the present disclosure is related to storage stable resin compositions, curable resin compositions obtainable therefrom, products obtainable from the latter, and uses thereof.
  • Curable resin compositions are widely known for various purposes.
  • One purpose of high interest is the use of curable resin compositions for electrical applications.
  • electrical devices such as instrument transformers, switchgears, insulators, bushings or DDTs, are manufactured by automated pressure gelation (APG) and/or vacuum casting processes of curable resin compositions which are then cured under suitable conditions.
  • APG automated pressure gelation
  • fillers are added to the curable resin compositions to obtain the necessary mechanical characteristics.
  • curable resin compositions are for impregnation of paper bushings for high-voltage applications or (vacuum pressure) impregnation of mica-tape used for insulating large generators and motors or of filament windings, e.g. of tubes for hollow core insulators.
  • Such compositions usually do not use fillers.
  • compositions and/or methods disclosed herein can be made and executed without undue experimentation in light of the present disclosure. While the compositions and methods of the present disclosure have been described in terms of preferred embodiments, it will be apparent to those having ordinary skill in the art that variations may be applied to the compositions and/or methods and in the steps or sequences of steps of the methods described herein without departing from the concept, spirit, and scope of the present disclosure. All such similar substitutes and modifications apparent to those skilled in the art are deemed to be within the spirit, scope, and concept of the present disclosure.
  • the term “about” is used to indicate that a value includes the inherent variation of error for the quantifying device, mechanism, or method, or the inherent variation that exists among the subject(s) to be measured.
  • the designated value to which it refers may vary by plus or minus ten percent, or nine percent, or eight percent, or seven percent, or six percent, or five percent, or four percent, or three percent, or two percent, or one percent, or one or more fractions therebetween.
  • At least one will be understood to include one as well as any quantity more than one, including but not limited to, 1, 2, 3, 4, 5, 10, 15, 20, 30, 40, 50, 100, etc.
  • the term “at least one” may extend up to 100 or 1000 or more depending on the term to which it refers. In addition, the quantities of 100/1000 are not to be considered as limiting since lower or higher limits may also produce satisfactory results.
  • the words “comprising” (and any form of comprising, such as “comprise” and “comprises”), “having” (and any form of having, such as “have” and “has”), “including” (and any form of including, such as “includes” and “include”) or “containing” (and any form of containing, such as “contains” and “contain”) are inclusive or open-ended and do not exclude additional, unrecited elements or method steps.
  • phrases “or combinations thereof” and “and combinations thereof” as used herein refers to all permutations and combinations of the listed items preceding the term.
  • “A, B, C, or combinations thereof” is intended to include at least one of: A, B, C, AB, AC, BC, or ABC and, if order is important in a particular context, also BA, CA, CB, CBA, BCA, ACB, BAC, or CAB.
  • expressly included are combinations that contain repeats of one or more items or terms such as BB, AAA, CC, AABB, AACC, ABCCCC, CBBAAA, CABBB, and so forth.
  • the present disclosure is related to a storage stable resin composition, comprising an epoxy resin, a block-copolymer with silicone and organic blocks, and a silane.
  • the epoxy resin is a bisphenol-A epoxy resin.
  • the storage stable resin composition contains the block-copolymer in an amount of 4 to 8 wt. %, based on the sum of amounts of the epoxy resin, the block-copolymer and the silane.
  • the storage stable resin composition contains the block-copolymer in an amount of 5 to 8 wt. %, more preferably 5.5 to 8 wt. %, based on the sum of amounts of the epoxy resin, the block-copolymer and the silane.
  • the silane is an epoxy silane.
  • the storage stable resin composition contains the silane in an amount of 0.6 to 1.5 wt. %, based on the sum of amounts of the epoxy resin, the block-copolymer and the silane.
  • the present disclosure is also related to a process for obtaining the presently disclosed storage stable resin composition, wherein the epoxy resin is blended with the block-copolymer at a temperature of 80° C. or more, preferably between 80 and 120° C., most preferably between 80 and 100° C. to obtain a blend, the blend is cooled down to a temperature of 60° C. or below, preferably between 60 and 40° C., and then mixed with the silane.
  • the present disclosure is also related to a curable resin composition comprising the presently disclosed storage stable resin composition and a hardener component.
  • the hardener component is based on an anhydride, an amine, a dicyandiamide, or a catalyst that triggers epoxy polymerization.
  • the curable resin composition additionally comprises a filler component.
  • the curable resin composition comprises the filler component in an amount of 60 to 70 wt. %, based on the sum of amounts of the epoxy resin, the block-copolymer, the silane, the hardener and the filler component.
  • the filler component comprises silica, most preferably in a content of 50 to 100 wt. %, or alternatively 50 to 90 wt. %, or alternatively 60 to 90 wt. %, or alternatively to 60 to 70 wt. %, or alternatively 70 to 80 wt%, based on the sum of the constituents of the filler component.
  • the curable resin composition additionally comprises additives, such as curing accelerators, flexibilizers, coloring agents, anti-settling agents or deforming agents.
  • the present disclosure also relates to a cured article obtainable by curing the presently disclosed curable resin composition.
  • the present disclosure is also related to the use of the presently disclosed cured article for electrical applications, such as instrument transformers, switchgears, insulators, bushings, hollow core insulators or dry-type distribution transformers.
  • the present disclosure is still further related to one or more of an instrument transformer, switchgear, insulator, bushing, hollow core insulator, or dry-type distribution transformer containing a cured article obtained by curing the curable resin composition as disclosed herein.
  • the present disclosure is related to the use of the presently disclosed curable resin composition (without filler) for impregnation of paper bushings for high-voltage applications or for impregnation of mica-tape or filament windings of insulated large generators and motors.
  • the present disclosure is also related to paper bushings for high-voltage applications and/or mica-tape or filament windings, which have been impregnated with the presently disclosed curable resin composition.
  • the present disclosure is related to the use of the curable resin composition as disclosed herein for encapsulation of stators of electrical motors, in particular for use in electric vehicles.
  • compositions of the present disclosure also show a lower viscosity (both with and without filler), a better impregnation performance, and a better thermal aging stability at predictably lower production costs.
  • the epoxy resin used for the presently disclosed curable resin composition may be any kind of epoxy resin without any specific limitation.
  • the epoxy resin may, for example, be a polyglycidylether, a cycloaliphatic epoxy resin or an N-glycidyl compound.
  • the polyglycidylether may, for example, be selected from bisphenol-A-diglycidylether, bisphenol-F-diglycidylether, 2,2-bis(4-hydroxy-3-methylphenyl)propane-diglycidylether, bisphenol-E-diglycidylether, 2,2-bis(4-hydroxyphenyl)butane-diglycidyl-ether, bis(4-hydroxyphenyl)-2,2-dichloro-ethylene, bis(4-hydroxyphenyl)diphenylmethane-diglycidylether, 9,9-bis(4-hydroxyphenyl)fluorene-diglycidylether, 4,4′-cyclohexylidenebisphenol-diglycidyl-ether, epoxy phenol novolac, epoxy cresol novolac, or combinations thereof.
  • the cycloaliphatic epoxy resin may, for example, be selected from bis(epoxycyclohexyl)-methylcarboxylate, bis(4-hydroxy-cyclohexyl)methane-diglycidylether, 2,2-bis(4-hydroxy-cyclohexyl)propane-diglycidylether, tetrahydrophthalicacid-diglycidylester, hexahydrophthalicacid-diglycidylester, 4-methyltetrahydrophthalicacid-diglycidylester, 4-methylhexahydrophthalicacid-diglycidylester, or combinations thereof.
  • the N-glycidyl compound may be selected, for example, from N,N,N′,N′-tetraglycidyl-4,4′-methylene-bis-benzeneamine, N,N,N′,N′-tetraglycidyl-3,3′-diethyl -4,4′-diamino-diphenylmethane, 4,4′-methylene-bis[N,N-bis(2,3-epoxypropyl)aniline], 2,6-dimethyl-N,N-bis[(oxiran-2-yl)methyl]aniline, or combinations thereof.
  • Specifically preferred epoxy resins are polyglycidyl ethers based on bisphenol, such as bisphenol-A-diglycidyl ether.
  • any silane suitable for use with epoxy resins may be incorporated into the composition. Because of specifically high compatibility with the epoxy resin, an epoxy silane may be chosen.
  • any filler suitable for the respective application is appropriate.
  • metal powder, wood powder, glass powder, glass spheres, semimetal and metal oxides such as, for example, SiO 2 (quartz sand, silica powder, fused silica), aluminum oxide, titanium oxide and zirconium oxide, metal hydroxides such as MgOH 2 , AlOH 3 and AlO(OH), semimetal and metal nitrides such as, for example, silicon nitride, boron nitrides and aluminum nitride, semimetal and metal carbides such as, for example, SiC and boron carbides, metal carbonates such as, for example, dolomite, chalk, CaCO 3 , metal sulfates such as, for example, baryte and gypsum, stone powders and natural and synthetic minerals, in particular those from the group of silicates, such as, for example, zeolithes (in particular molecular sieve), silicon silica powder, fused silica), aluminum oxide,
  • a filler should, of course, not be used for such uses as impregnation of paper bushings for high-voltage applications or impregnation of mica-tape or filament windings of insulated large generators and motors, as a filler would block pores and prevent effective impregnation.
  • the results can be optimized by selecting the parameters of the process for obtaining the presently disclosed storage stable resin composition.
  • blending the epoxy resin and the block-copolymer at an elevated dispersion temperature of 80° C. or more, for example, between 80 and 120° C., most preferably, between 80 and 100° C. results in a specifically stable and homogenous dispersion.
  • the hardener component may be any of this type which is suitable for curing epoxy resin compositions.
  • examples are compounds based on anhydride, such as methyltetrahydrophthalic anhydride, or amine, such as the JEFFAMINE® polyetheramines available from Huntsman Corp. or an affiliate thereof (The Woodlands, Tex.), or dicyandiamide (“dicy”), such as Dyhard® 100S from Alzchem (Trostberg, Germany), or on a catalyst, for example a cationic catalyst, such as dibenzylphenylsulfonium-hexafluoroantimonate, that triggers polymerization.
  • anhydride such as methyltetrahydrophthalic anhydride
  • amine such as the JEFFAMINE® polyetheramines available from Huntsman Corp. or an affiliate thereof (The Woodlands, Tex.)
  • dicyandiamide (“dicy”) such as Dyhard® 100S from Alzchem (Trostberg, Germany)
  • Non-limiting examples of amines suitable as a hardener include include benzenediamine, 1,3-diaminobenzene; 1,4-diaminobenzene; 4,4′-diamino-diphenylmethane; polyaminosulphones, such as 4,4′-diaminodiphenyl sulphone (4,4′-DDS), 4-aminophenyl sulphone, and 3,3′-diaminodiphenyl sulphone (3,3′-DDS); dicyanpolyamides, such as dicyandiamide; imidazoles; 4,4′-methylenedianiline; bis(4-amino-3,5-dimethylphenyl)-1,4-diisopropylbenzene; bis(4-aminophenyl)-1,4-diisopropylbenzene; ethylenediamine (EDA); 4,4′-methylenebis-(2,6-diethyl)-
  • Non-limiting examples of anhydrides suitable as a hardener include polycarboxylic anhydrides, such as nadic anhydride, methylnadic anhydride, phthalic anhydride, tetrahydrophthalic anhydride, hexahydrophthalic anhydride, methyltetrahydrophthalic anhydride, methylhexahydrophthalic anhydride, endomethylenetetrahydrophthalic anhydride, hexachloroendomethylene-tetrahydrophthalic anhydride, trimellitic anhydride, pyromellitic dianhydride, maleic anhydride, succinic anhydride, nonenylsuccinic anhydride, dodecenylsuccinic anhydride, polysebacic polyanhydride, and polyazelaic polyanhydride.
  • polycarboxylic anhydrides such as nadic anhydride, methylnadic anhydride, phthalic anhydride, te
  • the viscosity of the mixture was measured at 60 and 80° C.
  • reaction mass was then poured into a mold (preheated to 100° C.) to prepare plates for the mechanical test.
  • the mold was put to an oven for 2 hours at 100° C. and 16 hours at 140° C.
  • the plates were machined into test specimens and subjected to determine the mechanical parameters (tensile test, toughness, coefficient of thermal expansion (CTE) and Tg (via Differential Scanning Calorimetry (DSC) according to ISO 11357-2).
  • reaction mass was then poured into a mold (preheated to 100° C.) to prepare plates for the mechanical test.
  • the mold was put to an oven for 2 hours at 100° C. and 16 hours at 140° C.
  • the plates were machined into test specimens and subjected to determine the mechanical parameters (tensile test, toughness, CTE and Tg (via DSC) according to ISO 11357-2).
  • reaction mass was then poured into a mold (preheated to 100° C.) to prepare plates for the mechanical test.
  • the mold was put to an oven for 2 hours at 100° C. and 16 hours at 140° C.
  • the plates were machined into test specimens and subjected to determine the mechanical parameters (tensile test, toughness, CTE and Tg (via DSC) according to ISO 11357-2).
  • reaction mass was then poured in a mold (preheated to 100° C.) to prepare plates for the mechanical test.
  • the mold was put to an oven for 2 hours at 100° C. and 16 hours at 140° C.
  • the plates were machined into test specimens and subjected to determine the mechanical parameters (tensile test, toughness, CTE and Tg (via DSC) according to ISO 11357-2).
  • the viscosity of the mixture was measured at 60 and 80° C.
  • reaction mass was then poured into a mold (preheated to 100° C.) to prepare plates for the mechanical test.
  • the mold was put to an oven for 2 hours at 100° C. and 16 hours at 140° C.
  • the plates were machined into test specimens and subjected to determine the mechanical parameters (tensile test, toughness, CTE and Tg (via DSC) according to ISO 11357-2).
  • reaction mass was then poured into a mold (preheated to 100° C.) to prepare plates for the mechanical test.
  • the mold was put to an oven for 2 hours at 100° C. and 16 hours at 140° C.
  • the plates were machined into test specimens and subjected to determine the mechanical parameters (tensile test, toughness, CTE and Tg (via DSC) according to ISO 11357-2).
  • reaction mass was then poured into a mold (preheated to 100° C.) to prepare plates for the mechanical test.
  • the mold was put to an oven for 2 hours at 100° C. and 16 hours at 140° C.
  • the plates were machined into test specimens and subjected to determine the mechanical parameters (tensile test, toughness, CTE and Tg (via DSC) according to ISO 11357-2).
  • reaction mass was then poured into a mold (preheated to 100° C.) to prepare plates for the mechanical test.
  • the mold was put to an oven for 2 hours at 100° C. and 16 hours at 140° C.
  • the plates were machined into test specimens and subjected to determine the mechanical parameters (tensile test, toughness, CTE and Tg (via DSC) according to ISO 11357-2).
  • the simulated crack temperature was calculated in the same way as explained in EP 1 165 688 A1.
  • the formula is:

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Epoxy Resins (AREA)
  • Processes Of Treating Macromolecular Substances (AREA)
US16/981,334 2018-03-16 2019-03-14 Storage Stable and Curable Resin Compositions Pending US20210009803A1 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
EP18162350 2018-03-16
EP18162350.5 2018-03-16
PCT/EP2019/056473 WO2019175342A1 (en) 2018-03-16 2019-03-14 Storage stable and curable resin compositions

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US20210009803A1 true US20210009803A1 (en) 2021-01-14

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US (1) US20210009803A1 (ja)
EP (1) EP3765567A1 (ja)
JP (1) JP7411587B2 (ja)
KR (1) KR20200133267A (ja)
CN (1) CN111868170A (ja)
BR (1) BR112020018692B1 (ja)
CA (1) CA3092009A1 (ja)
MX (1) MX2020009610A (ja)
PH (1) PH12020551415A1 (ja)
WO (1) WO2019175342A1 (ja)

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US20220135862A1 (en) * 2019-04-11 2022-05-05 Huntsman Advanced Materials Licensing (Switzerland) Gmbh Curable Two-Component Resin-Based System
CA3203571A1 (en) 2020-12-22 2022-06-30 Huntsman Advanced Materials Licensing (Switzerland) Gmbh Curable two-part resin system

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JP7411587B2 (ja) 2024-01-11
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